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Details

Stereochemistry RACEMIC
Molecular Formula C4H6O5
Molecular Weight 134.0874
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Malic acid

SMILES

OC(CC(O)=O)C(O)=O

InChI

InChIKey=BJEPYKJPYRNKOW-UHFFFAOYSA-N
InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)

HIDE SMILES / InChI

Molecular Formula C4H6O5
Molecular Weight 134.0874
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Malic acid is a racemic mixture of naturally occuring L-malic acid and D-malic acid. Malic acid is used in cosmetic product formulations and is generally recognized as safe as a direct food additive for use as a flavor enhancer, flavoring agent and adjuvant, and as a pH control agent. In medicine malic acid is also used in the preparation of salts. The racemic malic acid is an active ingredient of Acerbine solution, which is applied for the treatment of superficial skin injuries. L-Malic acid is an intermediate of the Krebs cycle.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Curative
ACERBINE

Approved Use

Acerbine solution is suitable for the treatment of superficial skin injuries, such as burns, scalds, sunburn, wounds and abrasions.
PubMed

PubMed

TitleDatePubMed
Metabolic regulation of pH in plant cells: role of cytoplasmic pH in defense reaction and secondary metabolism.
2001
Final report on the safety assessment of Malic Acid and Sodium Malate.
2001
Development of a new calcium phosphate cement that contains sodium calcium phosphate.
2001 Apr
Survey of normal appearing mouse strain which lacks malic enzyme and Nad+-linked glycerol phosphate dehydrogenase: normal pancreatic beta cell function, but abnormal metabolite pattern in skeletal muscle.
2001 Apr
Physiological basis of reduced AL tolerance in ditelosomic lines of Chinese Spring wheat.
2001 Apr
Inhibiting expression of a tomato ripening-associated membrane protein increases organic acids and reduces sugar levels of fruit.
2001 Apr
Reevaluating the free-ion activity model of trace metal toxicity toward higher plants: experimental evidence with copper and zinc.
2001 Apr
Phlebotomine sandflies in Venezuela. V. Review of the genus Brumptomyia (Diptera: Psychodidae), with description of the female of Brumptomyia devenanzii, re-description of the male and isozymatic profile.
2001 Apr
Carbohydrate deprivation reduces NADPH-production in fish liver but not in adipose tissue.
2001 Aug
Characterization of a novel complex from halophilic archaebacteria, which displays chaperone-like activities in vitro.
2001 Aug 10
Alteration of the specificity of malate dehydrogenase by chemical modulation of an active site arginine.
2001 Aug 17
Substrate and cofactor binding to fluorescently labeled cytoplasmic malate dehydrogenase.
2001 Feb 9
[Lactate and malate dehydrogenase activity in the sterlet and Russian sturgeon under conditions of the widespread muscular pathology].
2001 Jan-Feb
Thyroid hormone--sympathetic interaction and adaptive thermogenesis are thyroid hormone receptor isoform--specific.
2001 Jul
Massive sequence comparisons as a help in annotating genomic sequences.
2001 Jul
Altered expression and function of mitochondrial beta-oxidation enzymes in juvenile intrauterine-growth-retarded rat skeletal muscle.
2001 Jul
Ergosteroids IV: synthesis and biological activity of steroid glucuronosides, ethers, and alkylcarbonates.
2001 Jul
Relationships between inhibition constants, inhibitor concentrations for 50% inhibition and types of inhibition: new ways of analysing data.
2001 Jul 1
pH-dependent investigations of vanadium(V)-peroxo-malate complexes from aqueous solutions. In search of biologically relevant vanadium(V)-peroxo species.
2001 Jul 16
Transcriptome meets metabolome: hierarchical and metabolic regulation of the glycolytic pathway.
2001 Jul 6
The effect of nucleotides and mitochondrial chaperonin 10 on the structure and chaperone activity of mitochondrial chaperonin 60.
2001 Jun
Aluminum speciation studies in biological fluids. Part 7. A quantitative investigation of aluminum(III)-malate complex equilibria and their potential implications for aluminum metabolism and toxicity.
2001 Jun
Oral almotriptan vs. oral sumatriptan in the abortive treatment of migraine: a double-blind, randomized, parallel-group, optimum-dose comparison.
2001 Jun
Energetic determinants of tyrosine phosphorylation of focal adhesion proteins during hypoxia/reoxygenation of kidney proximal tubules.
2001 Jun
A pre-genetic study of the isoforms of malic enzyme associated with lipid accumulation in Mucor circinelloides.
2001 Jun
What controls the outer mitochondrial membrane permeability for ADP: facts for and against the role of oncotic pressure.
2001 Jun 1
Myoadenylate deaminase deficiency does not affect muscle anaplerosis during exhaustive exercise in humans.
2001 Jun 15
Histochemical study of acute and chronic intraperitoneal nicotine effects on several glycolytic and Krebs cycle dehydrogenase activities in the frontoparietal cortex and subcortical nuclei of the rat brain.
2001 Jun 15
An NMR-based metabonomic approach to the investigation of coelomic fluid biochemistry in earthworms under toxic stress.
2001 Jun 29
The homeodomain proteins PBX and MEIS1 are accessory factors that enhance thyroid hormone regulation of the malic enzyme gene in hepatocytes.
2001 Jun 29
Non-photosynthetic 'malic enzyme' from maize: a constituvely expressed enzyme that responds to plant defence inducers.
2001 Mar
Relationship between NADP-specific isocitrate dehydrogenase and glutathione peroxidase in aging rat skeletal muscle.
2001 Mar
A study into the role of L-aspartic acid on the metabolism of L-malic acid and D-glucose by Oenococcus oeni.
2001 Mar
[Properties of gluconeogenesis enzymes from flatworms].
2001 Mar-Apr
Production of beta-thujaplicin in Cupressus lusitanica suspension cultures fed with organic acids and monoterpenes.
2001 May
New phenolic constituents from the fruit juice of Phyllanthus emblica.
2001 May
Comprehensive chemical profiling of gramineous plant root exudates using high-resolution NMR and MS.
2001 May
Cloning and functional characterization of the 5' flanking region of the human mitochondrial malic enzyme gene. Regulatory role of Sp1 and AP-2.
2001 May
Possible involvement of protein phosphorylation in aluminum-responsive malate efflux from wheat root apex.
2001 May
Aluminum activates a citrate-permeable anion channel in the aluminum-sensitive zone of the maize root apex. A comparison between an aluminum- sensitive and an aluminum-resistant cultivar.
2001 May
Oxyconformity in the intertidal worm Sipunculus nudus: the mitochondrial background and energetic consequences.
2001 May
Amide hydrogen exchange shows that malate dehydrogenase is a folded monomer at pH 5.
2001 May
High frequency of cytolytic T lymphocytes directed against a tumor-specific mutated antigen detectable with HLA tetramers in the blood of a lung carcinoma patient with long survival.
2001 May 1
Determination of organic acids and inorganic anions in wine by isotachophoresis on a planar chip.
2001 May 4
Enzymatic computing.
2001 May-Jun
Assimilation of D-malate by Rhodobacter capsulatus E1F1.
2001 Sep
[Isoenzyme patterns of the isolates of Blastocystis hominis from Guangxi].
2010 Feb
Method validation and determinations of levofloxacin, metronidazole and sulfamethoxazole in an aqueous pharmaceutical, urine and blood plasma samples using quantitative nuclear magnetic resonance spectrometry.
2012 Jan 15
The virucidal effect against murine norovirus and feline calicivirus as surrogates for human norovirus by ethanol-based sanitizers.
2013 Aug
The virucidal effects against murine norovirus and feline calicivirus F4 as surrogates for human norovirus by the different additive concentrations of ethanol-based sanitizers.
2016 Mar
Patents

Sample Use Guides

Oral lethal dose of Sodium Malate in dogs was 1 g/kg
Route of Administration: Oral
The effects of two concentrations of disodium malate on the in vitro fermentation of three substrates differing in their forage : concentrate ratio (0.8 : 0.2, 0.5 : 0.5 and 0.2 : 0.8; g/g dry matter; low-, medium- and high-concentrate substrates, respectively) by rumen micro-organisms were studied using batch cultures. Rumen contents were collected from four Merino sheep offered lucerne hay ad libitum and supplemented daily with 400 g concentrate. Disodium malate was added to the incubation bottles to achieve final concentrations of 0, 4 and 8 mmol/l malate and 15N was used as a microbial marker.
Substance Class Chemical
Created
by admin
on Fri Dec 16 16:32:53 UTC 2022
Edited
by admin
on Fri Dec 16 16:32:53 UTC 2022
Record UNII
817L1N4CKP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Malic acid
EP   FCC   II   INCI   MI   NF   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
MALIC ACID [USP IMPURITY]
Common Name English
MALIC ACID, DL-
Common Name English
POMALOUS ACID
Common Name English
INS NO.296
Code English
MALIC ACID [VANDF]
Common Name English
MALATE
Common Name English
MALIC ACID [INCI]
Common Name English
MALIC ACID [USP-RS]
Common Name English
DL-MALIC ACID
Common Name English
HYDROXYBUTANEDIOIC ACID, (±)-
Systematic Name English
MALIC ACID [FCC]
Common Name English
E-296
Code English
NSC-25941
Code English
INS NO. 296
Code English
E296
Code English
(±)-MALIC ACID
Common Name English
MALIC ACID [II]
Common Name English
MALIC ACID [EP MONOGRAPH]
Common Name English
HYDROXYBUTANEDIOIC ACID [HSDB]
Common Name English
INS-296
Code English
MALIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC]
Common Name English
D,L-MALIC ACID
Common Name English
Malic acid [WHO-DD]
Common Name English
HYDROXYSUCCINIC ACID
Common Name English
MALIC ACID [MI]
Common Name English
2-HYDROXYBUTANEDIOIC ACID
Systematic Name English
MALIC ACID [NF]
Common Name English
Classification Tree Code System Code
CODEX ALIMENTARIUS (GSFA) INS-296
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
DSLD 2323 (Number of products:281)
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
JECFA EVALUATION INS-296
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
LOINC 13770-3
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
LOINC 25113-2
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
JECFA EVALUATION DL-MALIC ACID
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
CFR 21 CFR 184.1069
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
EPA PESTICIDE CODE 51101
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
LOINC 75068-7
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
Code System Code Type Description
NSC
25941
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
RXCUI
70612
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
ALTERNATIVE
HSDB
1202
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
DRUG BANK
DB12751
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
MESH
C030298
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
CAS
617-48-1
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
SUPERSEDED
RXCUI
29209
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
NCI_THESAURUS
C80654
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
CONCEPT Industrial Aid
WIKIPEDIA
MALIC ACID
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
CHEBI
30797
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
ECHA (EC/EINECS)
210-514-9
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
EPA CompTox
DTXSID0027640
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
RS_ITEM_NUM
1374601
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
CHEBI
15595
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
FDA UNII
817L1N4CKP
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
PUBCHEM
525
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
DAILYMED
817L1N4CKP
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
CHEBI
6650
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
EVMPD
SUB14455MIG
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
JECFA MONOGRAPH
INS-296
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
MERCK INDEX
M7041
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY Merck Index
ChEMBL
CHEMBL1455497
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
CAS
6915-15-7
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
EVMPD
SUB59600
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
PRIMARY
ECHA (EC/EINECS)
230-022-8
Created by admin on Fri Dec 16 16:32:54 UTC 2022 , Edited by admin on Fri Dec 16 16:32:54 UTC 2022
ALTERNATIVE
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY